GB2456458A - Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins - Google Patents
Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins Download PDFInfo
- Publication number
- GB2456458A GB2456458A GB0908598A GB0908598A GB2456458A GB 2456458 A GB2456458 A GB 2456458A GB 0908598 A GB0908598 A GB 0908598A GB 0908598 A GB0908598 A GB 0908598A GB 2456458 A GB2456458 A GB 2456458A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butene
- isomerization
- ionic liquid
- stream
- olefins
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title abstract 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 title abstract 5
- 238000006317 isomerization reaction Methods 0.000 title abstract 3
- 150000001336 alkenes Chemical class 0.000 title abstract 2
- 230000029936 alkylation Effects 0.000 title abstract 2
- 238000005804 alkylation reaction Methods 0.000 title abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 abstract 2
- 239000011831 acidic ionic liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
- C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
- C10G69/12—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step
- C10G69/123—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step alkylation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C9/00—Aliphatic saturated hydrocarbons
- C07C9/14—Aliphatic saturated hydrocarbons with five to fifteen carbon atoms
- C07C9/16—Branched-chain hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
- C10G29/205—Organic compounds not containing metal atoms by reaction with hydrocarbons added to the hydrocarbon oil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1081—Alkanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1088—Olefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/02—Gasoline
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/20—C2-C4 olefins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
A process for producing alkylate comprising contacting a first hydrocarbon stream comprising at least one olefin having from 2 to 6 carbon atoms which contains 1-butene with an isomerization catalyst under conditions favoring the isomerization of 1-butene to 2-butene so the isomerized stream contains a greater concentration of 2-butene than the first hydrocarbon stream and contacting the isomerized stream and a second hydrocarbon steam comprising at least one isoparaffin having from 3 to 6 carbon atoms with an acidic ionic liquid catalyst under alkylation conditions to produce an alkylate stream is disclosed.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/610,782 US7553999B2 (en) | 2006-12-14 | 2006-12-14 | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
PCT/US2007/087423 WO2008076823A1 (en) | 2006-12-14 | 2007-12-13 | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
Publications (4)
Publication Number | Publication Date |
---|---|
GB0908598D0 GB0908598D0 (en) | 2009-06-24 |
GB2456458A8 GB2456458A8 (en) | 2009-07-22 |
GB2456458A true GB2456458A (en) | 2009-07-22 |
GB2456458B GB2456458B (en) | 2012-02-15 |
Family
ID=39528302
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB0908598.6A Active GB2456458B (en) | 2006-12-14 | 2007-12-13 | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
GBGB1121730.4A Ceased GB201121730D0 (en) | 2006-12-14 | 2011-12-16 | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GBGB1121730.4A Ceased GB201121730D0 (en) | 2006-12-14 | 2011-12-16 | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
Country Status (9)
Country | Link |
---|---|
US (3) | US7553999B2 (en) |
KR (1) | KR101472147B1 (en) |
CN (1) | CN101679142B (en) |
AU (1) | AU2007333963B2 (en) |
BR (1) | BRPI0718656B1 (en) |
DE (1) | DE112007002597T5 (en) |
GB (2) | GB2456458B (en) |
MY (1) | MY167210A (en) |
WO (1) | WO2008076823A1 (en) |
Families Citing this family (48)
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US7955495B2 (en) * | 2008-07-31 | 2011-06-07 | Chevron U.S.A. Inc. | Composition of middle distillate |
US8674159B2 (en) * | 2009-05-19 | 2014-03-18 | Chevron U.S.A. Inc. | Hydroconversion process with alkyl halide comprising at least 55 wt% halide |
WO2011006848A1 (en) | 2009-07-17 | 2011-01-20 | Shell Internationale Research Maatschappij B.V. | Method for revamping an hf or sulphuric acid alkylation unit and method for the procduction of alkylate |
CN102639469B (en) * | 2009-08-06 | 2014-07-02 | 中国石油大学(北京) | Process for preparing an alkylate |
EP2462090B1 (en) * | 2009-08-06 | 2017-06-28 | Shell Internationale Research Maatschappij B.V. | Method for revamping an hf or sulphuric acid alkylation unit |
CN102596859B (en) * | 2009-08-06 | 2014-04-23 | 中国石油大学(北京) | Method for revamping an HF or sulphuric acid alkylation unit |
US20110092753A1 (en) * | 2009-10-19 | 2011-04-21 | Bi-Zeng Zhan | Hydroisomerization and selective hydrogenation of feedstock in ionic liquid-catalyzed alkylation |
US8299311B2 (en) * | 2009-11-30 | 2012-10-30 | Chevron U.S.A. Inc. | Process for reacting iso-pentane |
US8247628B2 (en) | 2009-11-30 | 2012-08-21 | Chevron U.S.A. Inc. | Process for reacting iso-alkane |
CN102108306B (en) * | 2009-12-28 | 2013-12-18 | 中国石油大学(北京) | Alkylation reaction method using ionic liquid as catalyst |
US8455708B2 (en) | 2010-03-17 | 2013-06-04 | Chevron U.S.A. Inc. | Flexible production of alkylate gasoline and distillate |
US8487154B2 (en) * | 2010-03-17 | 2013-07-16 | Chevron U.S.A. Inc. | Market driven alkylation or oligomerization process |
US8895794B2 (en) * | 2010-03-17 | 2014-11-25 | Chevron U.S.A. Inc. | Process for producing high quality gasoline blending components in two modes |
US20110282114A1 (en) | 2010-05-14 | 2011-11-17 | Chevron U.S.A. Inc. | Method of feeding reactants in a process for the production of alkylate gasoline |
US8728301B2 (en) * | 2011-09-12 | 2014-05-20 | Chevron U.S.A. Inc. | Integrated butane isomerization and ionic liquid catalyzed alkylation processes |
DE102012214511A1 (en) | 2011-11-10 | 2013-05-16 | Leibniz-Institut Für Polymerforschung Dresden E.V. | Temperature resistant elastomeric materials useful e.g. as sealing material for heat stressed treatments, comprise diene rubber with double bonds and liquid with imidazolium salts distributed in diene rubbers and present around double bonds |
US9302199B2 (en) | 2012-07-31 | 2016-04-05 | Chevron U.S.A. Inc. | Alkylation process with recycle of hydrogen and recovery of hydrogen chloride |
US9233316B2 (en) | 2012-07-31 | 2016-01-12 | Chevron U.S.A. Inc. | Hydrogen recycle and hydrogen chloride recovery in an alkylation process |
US8704018B2 (en) | 2012-07-31 | 2014-04-22 | Chevron U.S.A. Inc. | Extracted conjunct polymer naphtha |
US9096481B2 (en) | 2013-06-28 | 2015-08-04 | Uop Llc | Catalytic disproportionation of pentane using ionic liquids |
US20150005555A1 (en) | 2013-06-28 | 2015-01-01 | Uop Llc | Catalytic disproportionation of butane using ionic liquids |
US9102578B2 (en) | 2013-06-28 | 2015-08-11 | Uop Llc | Catalytic isomerization of paraffins using ionic liquids |
US9096485B2 (en) | 2013-06-28 | 2015-08-04 | Uop Llc | Catalytic isomerization of heptane using ionic liquids |
US9096482B2 (en) | 2013-06-28 | 2015-08-04 | Uop Llc | Catalytic reverse disproportionation of paraffins using ionic liquids |
US9102577B2 (en) | 2013-06-28 | 2015-08-11 | Uop Llc | Catalytic disproportionation of paraffins using ionic liquids |
US9126881B2 (en) | 2013-06-28 | 2015-09-08 | Uop Llc | Catalytic isomerization of pentane using ionic liquids |
US9096483B2 (en) | 2013-06-28 | 2015-08-04 | Uop Llc | Catalytic isomerization of hexanes using ionic liquids |
US9096480B2 (en) | 2013-06-28 | 2015-08-04 | Uop Llc | Catalytic disproportionation of heptane using ionic liquids |
US9302951B2 (en) * | 2014-01-30 | 2016-04-05 | Uop Llc | Ionic liquid alkylation of 1-butene to produce 2,5-dimethylhexane |
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WO2019060219A1 (en) * | 2017-09-20 | 2019-03-28 | E. I. Du Pont De Nemours And Company | Alkylation with olefin mixtures |
KR102581907B1 (en) | 2018-01-02 | 2023-09-22 | 에스케이이노베이션 주식회사 | Method for manufacturing paraffin |
EP3768806A1 (en) | 2018-03-19 | 2021-01-27 | SABIC Global Technologies B.V. | Method of producing a fuel additive |
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US11697626B2 (en) | 2018-05-18 | 2023-07-11 | Sabic Global Technologies B.V. | Method of producing a fuel additive with a hydration unit |
CN112808305B (en) * | 2021-01-12 | 2022-12-16 | 山东新和成药业有限公司 | Catalytic system for catalyzing olefin isomerization reaction and application thereof |
CN115181585B (en) * | 2022-08-09 | 2023-11-07 | 中国石油大学(北京) | Alkane isomerization method based on ionic liquid catalysis |
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-
2006
- 2006-12-14 US US11/610,782 patent/US7553999B2/en active Active
-
2007
- 2007-12-13 MY MYPI20091973A patent/MY167210A/en unknown
- 2007-12-13 CN CN200780042708.1A patent/CN101679142B/en active Active
- 2007-12-13 BR BRPI0718656-8A patent/BRPI0718656B1/en active IP Right Grant
- 2007-12-13 DE DE112007002597T patent/DE112007002597T5/en not_active Ceased
- 2007-12-13 KR KR1020097011334A patent/KR101472147B1/en active IP Right Grant
- 2007-12-13 AU AU2007333963A patent/AU2007333963B2/en not_active Ceased
- 2007-12-13 WO PCT/US2007/087423 patent/WO2008076823A1/en active Search and Examination
- 2007-12-13 GB GB0908598.6A patent/GB2456458B/en active Active
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2009
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2011
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- 2011-12-16 GB GBGB1121730.4A patent/GB201121730D0/en not_active Ceased
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5304695A (en) * | 1993-02-22 | 1994-04-19 | Mobil Oil Corporation | Double bond isomerization of olefin-containing feeds with minimal oligomerization using permanently surface acidity deactivated zeolite catalysts |
US20060135839A1 (en) * | 2004-12-21 | 2006-06-22 | Cheveron U.S.A., Inc. | Alkylation process using chloroaluminate ionic liquid catalysts |
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GB0908598D0 (en) | 2009-06-24 |
DE112007002597T5 (en) | 2009-10-15 |
WO2008076823A1 (en) | 2008-06-26 |
US8198494B2 (en) | 2012-06-12 |
GB2456458A8 (en) | 2009-07-22 |
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BRPI0718656A2 (en) | 2013-11-19 |
US20110144399A1 (en) | 2011-06-16 |
KR101472147B1 (en) | 2014-12-12 |
US7553999B2 (en) | 2009-06-30 |
GB201121730D0 (en) | 2012-02-01 |
GB2456458B (en) | 2012-02-15 |
KR20090089355A (en) | 2009-08-21 |
US20090192339A1 (en) | 2009-07-30 |
BRPI0718656B1 (en) | 2022-04-05 |
CN101679142A (en) | 2010-03-24 |
US20080146858A1 (en) | 2008-06-19 |
AU2007333963B2 (en) | 2011-10-06 |
MY167210A (en) | 2018-08-13 |
AU2007333963A1 (en) | 2008-06-26 |
CN101679142B (en) | 2014-05-21 |
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